- 1. Chemical context
- 2. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) monohydrate, (1)
- 3. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) acetone monosolvate, (2)
- 4. Database survey
- 5. Synthesis and crystallization
- 6. Refinement
- Supporting information
- References
- 1. Chemical context
- 2. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) monohydrate, (1)
- 3. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) acetone monosolvate, (2)
- 4. Database survey
- 5. Synthesis and crystallization
- 6. Refinement
- Supporting information
- References
research communications
Crystal structures of the water and acetone monosolvates of bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate)
aCICECO, Chemistry Department, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal
*Correspondence e-mail: jafernandes@ua.pt
The crystal structures of bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) monohydrate, [Mn(C20H14N4)2](PF6)2·H2O, (1), and bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) acetone monosolvate, (2), [Mn(C20H14N4)2](PF6)2·CH3COCH3, are described. At 150 K, (1) and (2) have monoclinic (P21/c) and orthorhombic (C2221) symmetries, respectively. Both structures exhibit octahedrally coordinated MnII atoms and disorder. They display weak interactions, such as C—H⋯F, C—H⋯N, C—H⋯π, F⋯π and π–π. The twofold rotation axis in the molecule of (2) is coincident with a twofold rotation axis of the crystal.
Keywords: crystal structure; metalloligand; manganese; terpyridine.
1. Chemical context
The synthesis of new metal–organic frameworks (MOFs) can be achieved by several ways with different degrees of reaction control. One way of having a tighter control on the reactions is the use of metalloligands. A metalloligand is a kind of ligand in which the bonding capabilities of the ligand are combined with the directionallity of a metal centre (Halper et al., 2006; Kitagawa et al., 2006; Noro et al., 2005).
As it is found from a database survey (dedicated section below), there is already a considerable number of compounds of the type [M(Pyterpy)2n+] [Pyterpy = 4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]. However, no equivalent structure is found with Mn2+ as metallic centre. In order to fill this gap, we describe in the present report the of the water and acetone monosolvates of bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate).
2. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) monohydrate, (1)
2.1. Structural commentary
The ) comprises a dicationic coordination complex, two highly disordered hexafluoridophosphate charge-balancing anions, and a water molecule distributed among four general locations. The Mn2+ cation is distorted octahedrally coordinated by two κ3N-(4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine) ligands. One of these ligands is spatially disordered over two close, but distinct, locations, with a distribution of occupancies of 0.85:0.15. Concerning only the major contributor for the disordered ligand, we may say that the coordination environment around the metal cation resembles a highly distorted octahedron with the Mn—N distances in the 2.193 (4)–2.268 (4) Å range, and the cis and trans octahedral angles found in the intervals 71.99 (17)–117.68 (17) and 143.36 (15)–169.95 (18)°, respectively. The angle between the medium planes of the terpyridine moieties is 85.76 (14)°, and the angles between the medium planes of non-coordinating pyridines and the terpyridine to which they are attached are 7.9 (2) and 47.1 (3)° (see Table 1 for details).
of (1) (Fig. 1
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2.2. Supramolecular features
The structure of (1) is highly disordered, and the H atoms belonging to water molecules were not found. For this reason, the description of this structure cannot be thorough (see Fig. 2 for crystal packing). Nevertheless, many weak interactions are present in the namely C—H⋯F, C—H⋯N, C—H⋯π, F⋯π and π–π interactions (see Tables 2 and 3 for details). Additionally, there is a close relation between the disordered water molecules and the entities in their neighbourhoods. While the position of site O3W (occupancy 0.15) is incompatible with the position of N8 (occupancy 0.85) at 2.43 (3) Å, it is foreseeable that it donates a proton to N108 at 2.94 (3) Å. The position of O4W (occupancy 0.85) is also incompatible with the H123 position [occupancy 0.15, distance 1.95 (5) Å]. Other contact distances are in the limit of possible hydrogen-bonding interactions, namely O1W⋯F6B [occupancies 0.4 and 0.3333, distance 2.57 (2) Å], O4W⋯F3A [occupancies 0.1 and 0.6667, distance 2.63 (5) Å] and O4W⋯H23 [occupancies 0.1 and 0.85, distance 2.35 (5) Å]. These relations suggest the water molecule accomodates in the empty spaces left by the disordered organic moieties, or vice versa.
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3. Bis[4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine]manganese(II) bis(hexafluoridophosphate) acetone monosolvate, (2)
3.1. Structural commentary
Except for the type of the co-crystallizing solvent, compound (2) (Fig. 3) is very similar to (1). However, the molecule of (2) exhibits a twofold rotation axis which is coincident to the axis of the coordination complex, which passes through atoms N13, C109, C8, N2, Mn1, N4, C19, C20 and N6. Thus, the comprises one half of the dicationic coordination compound, one disordered charge balancing hexafluoridophosphate anion and half of an acetone molecule. In the cation, only one of the noncoordinating pyridine moieties is affected by disorder. Nevertheless, the geometrical environment around the metal cation is still a distorted octahedron (with a symmetry axis in one of the diagonals), with Mn—N distances in the 2.180 (13)–2.247 (11) Å range, and the cis and trans octahedral angles in the intervals 72.3 (3)–107.7 (5) and 144.7 (5)–180.0°, respectively. The angle between the medium planes of the terpyridine moieties is 89.5 (3)°, and the angles between the medium planes of non-coordinating pyridines and the terpyridine to which they are attached are 35.3 (non-disordered), 62.3 (12) and 65.8 (13)° (disordered) (see Table 4 for details).
3.2. Supramolecular features
Similarly to (1), in the structure of compound (2) (Fig. 4) there are a considerable number of weak interactions present, namely C—H⋯F, C—H⋯O, C—H⋯π, F⋯π and π–π interactions (see Tables 5 and 6 for details).
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4. Database survey
The use of the ligand Pyterpy [described by Constable et al. (2000)] as precursor of metalloligands has contributed for the synthesis of several complexes of the form [M(Pyterpy)2]n+(X−)n. The metal centres comprise metals with valence +2 of the first transition period, from Fe2+ to Zn2+, as well as Co3+, Ru2+ and Rh3+ (Groom & Allen, 2014). The charge-balancing anions are PF6−, NO3−, ClO4−, SCN− or [Fe(SCN)6]3− (Beves, Bray et al., 2008; Beves, Constable, Housecroft, Kepert, Neuburger et al., 2007; Beves, Dunphy et al., 2008; Constable et al., 2000, 2006; Ding et al., 2009; Indumathy et al., 2007; Mehrani et al., 2013; Morsali et al., 2009; Paul et al., 2004; Pitarch López et al., 2005; see Table 7 for details).
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All the cations exhibit a distorted octahedral geometry, with the Pyterpy ligands in a meridional coordination. Some of the crystal structures sharing the same anion are isotypical. This is the case of the nitrate-containing crystals of Fe2+, Co2+ and Ni2+ [Cambridge Structural Database (CSD; Groom & Allen, 2014) refcodes WOMXAX, VEYGIQ and OFUJUV] or the hexafluoridophosphate-containing crystals of Fe2+ and Ru2+ (OFUKEG and KITFEZ). Two different solvates of [Fe(Pyterpy)(PyterpyH)][Fe(SCN)6] are also isotypical (XIQFIN and XIQFEJ). Additionally, two structures of Fe2+ and Ru2+ have similar cell parameters, despite of not sharing the same anion (OFUKIK and UGEKEX). None of compounds described in this work is isotypical with a previously reported structure.
Until now the use of the metalloligand [M(Pyterpy)2n+] is still very limited. Some one-dimensional polymers are known (Beves, Constable et al., 2008; Yoshida et al., 2009; Beves, Constable, Housecroft, Kepert, Price et al., 2007). Among the oligomers we can find linear structures with three (Liu et al., 2014) or five metal coordination centres (Beves et al., 2009) and hexanuclear cyclic clusters (Liu et al., 2014; see Table 8 for details).
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5. Synthesis and crystallization
All the reactants were purchased from commercial suppliers and used as received.
5.1. 4′-(Pyridin-4-yl)-2,2′:6′,2′′-terpyridine
The ligand Pyterpy was synthesized by a mechanochemical reaction of 2-acetylpyridine, 4-pyridinecarboxaldehyde and NaOH, followed by refluxing with ammonium acetate in acetic acid for 24 h (Cave & Raston, 2001).
5.2. Title compounds
A solution of Pyterpy (132.7 mg, 0.42 mmol) in MeOH (50 mL) was added dropwise to a solution of [Mn(CH3COO)2]·4H2O (52.4 mg, 0.21 mmol) in 5 mL of water. The mixture refluxed at 338 K overnight to obtain a complete reaction. After this period, the solution was concentrated until a light-brown solid was obtained. The solid was filtrated and washed with water and ethanol to remove the impurities. The solid was dried at 333 K. Analysis calculated for [C40H28F12MnN8][PF6]2·H2O: C 47.97, H 3.22, N 11.19%; found: C 47.37, H 3.19, N 11.09%.
Suitable crystals for X-ray diffraction were obtained by diffusion of water into a solution of the title compound in acetone. Two types of crystals were harvested corresponding to two different solvates.
6. Refinement
Crystal data, data collection and structure .
details are summarized in Table 9
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H atoms bound to carbon were placed at their idealized positions and were included in the final structural model in riding-motion approximation, with C—H = 0.95 Å (aromatic C—H) or C—H = 0.98 Å (aliphatic C—H). The isotropic displacement parameters for these atoms were fixed at 1.2 times Ueq of the respective parent carbon atom. Some parts of the two crystal structures are subjected to spatial disorder.
In (1), the disorder affects one whole ligand which is placed over two close, but not coincident locations, with occupancies 0.85:0.15. The two crystallographically independent PF6− anions are distributed over four distinct orientations with coincidence of the central P atoms, and occupancies 2/3:1/3, 2/3:1/3. The P atoms were refined anisotropically, and the F atoms isotropically with a common Uiso. The water molecule of crystallization was distributed over four distinct locations, which were isotropically refined with a common Uiso, and total occupancy equal to 1. The H atoms of the solvent were not located, but were added in the formula unit.
In (2), the disorder in the organic ligand was limited to a terminal 4-pyridine moiety, which was refined anisotropically over two locations with equal occupancies. The sole PF6− in (2) was distributed among two locations with occupancies 0.6:0.4 with P-atoms not coincident in space. The overall quality of the crystal was not sufficient for a precise determination of the Flack parameter.
Supporting information
10.1107/S2056989015003503/hg5428sup1.cif
contains datablocks 1, 2. DOI:Structure factors: contains datablock 1. DOI: 10.1107/S2056989015003503/hg54281sup2.hkl
Structure factors: contains datablock 2. DOI: 10.1107/S2056989015003503/hg54282sup3.hkl
For both compounds, data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for (1); SHELXL97 (Sheldrick, 2008) for (2). For both compounds, molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Mn(C20H14N4)2](PF6)2·H2O | F(000) = 1988 |
Mr = 983.60 | Dx = 1.605 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.2389 (5) Å | Cell parameters from 4312 reflections |
b = 15.3506 (5) Å | θ = 2.3–21.7° |
c = 16.5549 (5) Å | µ = 0.50 mm−1 |
β = 99.3892 (17)° | T = 150 K |
V = 4071.5 (2) Å3 | Block, yellow |
Z = 4 | 0.12 × 0.08 × 0.08 mm |
Bruker APEXII CCD diffractometer | 5275 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.085 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | θmax = 25.4°, θmin = 2.7° |
Tmin = 0.953, Tmax = 0.960 | h = −19→19 |
44958 measured reflections | k = −18→17 |
7445 independent reflections | l = −19→17 |
Refinement on F2 | 78 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.089 | H-atom parameters constrained |
wR(F2) = 0.244 | w = 1/[σ2(Fo2) + (0.1065P)2 + 15.4857P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
7445 reflections | Δρmax = 0.98 e Å−3 |
608 parameters | Δρmin = −1.03 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn1 | 0.23762 (5) | 0.32425 (5) | 0.12734 (5) | 0.0275 (2) | |
C1 | 0.2558 (3) | 0.3471 (4) | 0.3199 (3) | 0.0346 (13) | |
H1 | 0.1969 | 0.3397 | 0.3092 | 0.042* | |
C2 | 0.2943 (4) | 0.3585 (4) | 0.3993 (3) | 0.0416 (15) | |
H2 | 0.2625 | 0.3604 | 0.4426 | 0.050* | |
C3 | 0.3804 (4) | 0.3672 (4) | 0.4151 (3) | 0.0427 (15) | |
H3 | 0.4087 | 0.3741 | 0.4697 | 0.051* | |
C4 | 0.4244 (3) | 0.3657 (4) | 0.3509 (3) | 0.0370 (13) | |
H4 | 0.4835 | 0.3715 | 0.3608 | 0.044* | |
C5 | 0.3820 (3) | 0.3557 (3) | 0.2717 (3) | 0.0249 (11) | |
C6 | 0.4226 (3) | 0.3574 (3) | 0.1976 (3) | 0.0238 (10) | |
C7 | 0.5077 (3) | 0.3676 (3) | 0.1992 (3) | 0.0290 (11) | |
H7 | 0.5443 | 0.3718 | 0.2501 | 0.035* | |
C8 | 0.5394 (3) | 0.3716 (3) | 0.1263 (3) | 0.0283 (11) | |
C9 | 0.4837 (3) | 0.3648 (3) | 0.0532 (3) | 0.0281 (11) | |
H9 | 0.5033 | 0.3662 | 0.0022 | 0.034* | |
C10 | 0.3995 (3) | 0.3559 (3) | 0.0556 (3) | 0.0259 (11) | |
C11 | 0.3337 (3) | 0.3549 (4) | −0.0184 (3) | 0.0300 (12) | |
C12 | 0.3511 (3) | 0.3682 (4) | −0.0969 (3) | 0.0376 (14) | |
H12 | 0.4070 | 0.3751 | −0.1059 | 0.045* | |
C13 | 0.2859 (4) | 0.3713 (4) | −0.1616 (4) | 0.0439 (15) | |
H13 | 0.2965 | 0.3822 | −0.2154 | 0.053* | |
C14 | 0.2048 (4) | 0.3586 (4) | −0.1479 (3) | 0.0408 (14) | |
H14 | 0.1592 | 0.3599 | −0.1918 | 0.049* | |
C15 | 0.1922 (3) | 0.3440 (4) | −0.0678 (3) | 0.0359 (13) | |
H15 | 0.1370 | 0.3346 | −0.0577 | 0.043* | |
C16 | 0.7731 (4) | 0.3864 (5) | 0.1888 (4) | 0.0526 (18) | |
H16 | 0.8130 | 0.3756 | 0.2364 | 0.063* | |
C17 | 0.6904 (4) | 0.3686 (5) | 0.1921 (4) | 0.0511 (18) | |
H17 | 0.6751 | 0.3452 | 0.2406 | 0.061* | |
C18 | 0.6299 (3) | 0.3849 (4) | 0.1250 (3) | 0.0313 (12) | |
C19 | 0.6575 (4) | 0.4209 (5) | 0.0581 (4) | 0.0488 (16) | |
H19 | 0.6187 | 0.4355 | 0.0106 | 0.059* | |
C20 | 0.7424 (4) | 0.4359 (5) | 0.0600 (4) | 0.0577 (19) | |
H20 | 0.7598 | 0.4609 | 0.0131 | 0.069* | |
N1 | 0.2981 (3) | 0.3460 (3) | 0.2567 (3) | 0.0279 (9) | |
N2 | 0.3699 (3) | 0.3521 (3) | 0.1267 (3) | 0.0267 (9) | |
N3 | 0.2550 (3) | 0.3426 (3) | −0.0048 (3) | 0.0290 (10) | |
N4 | 0.8001 (3) | 0.4173 (4) | 0.1237 (3) | 0.0484 (14) | |
C21 | 0.3152 (3) | 0.1327 (4) | 0.1204 (8) | 0.0301 (13) | 0.85 |
H21 | 0.3661 | 0.1641 | 0.1243 | 0.036* | 0.85 |
C22 | 0.3177 (4) | 0.0437 (4) | 0.1137 (8) | 0.0398 (16) | 0.85 |
H22 | 0.3689 | 0.0141 | 0.1125 | 0.048* | 0.85 |
C23 | 0.2438 (4) | −0.0015 (5) | 0.1086 (8) | 0.0507 (19) | 0.85 |
H23 | 0.2433 | −0.0632 | 0.1038 | 0.061* | 0.85 |
C24 | 0.1706 (4) | 0.0433 (4) | 0.1104 (8) | 0.0450 (17) | 0.85 |
H24 | 0.1194 | 0.0126 | 0.1073 | 0.054* | 0.85 |
C25 | 0.1721 (3) | 0.1329 (4) | 0.1167 (6) | 0.0295 (13) | 0.85 |
C26 | 0.0960 (3) | 0.1864 (4) | 0.1156 (6) | 0.0311 (14) | 0.85 |
C27 | 0.0159 (4) | 0.1533 (4) | 0.1074 (4) | 0.0333 (17) | 0.85 |
H27 | 0.0070 | 0.0921 | 0.1069 | 0.040* | 0.85 |
C29 | −0.0365 (3) | 0.2992 (5) | 0.1051 (4) | 0.0332 (18) | 0.85 |
H29 | −0.0815 | 0.3393 | 0.1004 | 0.040* | 0.85 |
C30 | 0.0456 (3) | 0.3287 (4) | 0.1172 (6) | 0.0295 (14) | 0.85 |
C31 | 0.0684 (3) | 0.4218 (4) | 0.1253 (7) | 0.0288 (13) | 0.85 |
C32 | 0.0107 (4) | 0.4877 (4) | 0.1306 (8) | 0.037 (2) | 0.85 |
H32 | −0.0469 | 0.4745 | 0.1274 | 0.045* | 0.85 |
C33 | 0.0385 (4) | 0.5721 (5) | 0.1407 (4) | 0.039 (2) | 0.85 |
H33 | 0.0001 | 0.6181 | 0.1442 | 0.047* | 0.85 |
C34 | 0.1223 (4) | 0.5897 (4) | 0.1456 (10) | 0.039 (2) | 0.85 |
H34 | 0.1424 | 0.6478 | 0.1524 | 0.047* | 0.85 |
C35 | 0.1759 (4) | 0.5220 (4) | 0.1405 (15) | 0.0365 (15) | 0.85 |
H35 | 0.2337 | 0.5344 | 0.1440 | 0.044* | 0.85 |
N5 | 0.2449 (3) | 0.1775 (3) | 0.1218 (7) | 0.0268 (10) | 0.85 |
N6 | 0.1094 (3) | 0.2730 (3) | 0.1208 (6) | 0.0267 (10) | 0.85 |
N7 | 0.1508 (3) | 0.4387 (3) | 0.1308 (9) | 0.0282 (16) | 0.85 |
C28 | −0.0515 (4) | 0.2103 (5) | 0.0998 (4) | 0.0295 (15) | 0.85 |
C36 | −0.2505 (6) | 0.0891 (6) | 0.1153 (6) | 0.055 (2) | 0.85 |
H36 | −0.2682 | 0.0424 | 0.1460 | 0.066* | 0.85 |
C37 | −0.1654 (4) | 0.1106 (5) | 0.1289 (5) | 0.0437 (17) | 0.85 |
H37 | −0.1266 | 0.0786 | 0.1667 | 0.052* | 0.85 |
C38 | −0.1400 (4) | 0.1792 (5) | 0.0859 (4) | 0.0362 (15) | 0.85 |
C39 | −0.1991 (4) | 0.2225 (5) | 0.0295 (5) | 0.0427 (17) | 0.85 |
H39 | −0.1833 | 0.2700 | −0.0015 | 0.051* | 0.85 |
C40 | −0.2812 (4) | 0.1948 (5) | 0.0196 (5) | 0.0455 (18) | 0.85 |
H40 | −0.3209 | 0.2237 | −0.0200 | 0.055* | 0.85 |
N8 | −0.3080 (4) | 0.1298 (4) | 0.0623 (4) | 0.0504 (16) | 0.85 |
C121 | 0.3340 (10) | 0.1304 (9) | 0.125 (5) | 0.0301 (13) | 0.15 |
H121 | 0.3835 | 0.1642 | 0.1291 | 0.036* | 0.15 |
C122 | 0.3405 (11) | 0.0416 (10) | 0.119 (5) | 0.0398 (16) | 0.15 |
H122 | 0.3932 | 0.0143 | 0.1208 | 0.048* | 0.15 |
C123 | 0.2683 (11) | −0.0068 (9) | 0.112 (5) | 0.0507 (19) | 0.15 |
H123 | 0.2702 | −0.0682 | 0.1053 | 0.061* | 0.15 |
C124 | 0.1933 (11) | 0.0343 (8) | 0.114 (5) | 0.0450 (17) | 0.15 |
H124 | 0.1435 | 0.0012 | 0.1113 | 0.054* | 0.15 |
C125 | 0.1911 (8) | 0.1238 (7) | 0.122 (3) | 0.0295 (13) | 0.15 |
C126 | 0.1131 (8) | 0.1734 (6) | 0.123 (3) | 0.0311 (14) | 0.15 |
C127 | 0.0362 (10) | 0.1360 (7) | 0.126 (3) | 0.0333 (17) | 0.15 |
H127 | 0.0326 | 0.0743 | 0.1275 | 0.040* | 0.15 |
C129 | −0.0227 (9) | 0.2790 (9) | 0.126 (3) | 0.0332 (18) | 0.15 |
H129 | −0.0685 | 0.3174 | 0.1266 | 0.040* | 0.15 |
C130 | 0.0565 (7) | 0.3130 (7) | 0.125 (3) | 0.0295 (14) | 0.15 |
C131 | 0.0750 (7) | 0.4073 (7) | 0.130 (4) | 0.0288 (13) | 0.15 |
C132 | 0.0134 (8) | 0.4711 (7) | 0.119 (5) | 0.037 (2) | 0.15 |
H132 | −0.0439 | 0.4556 | 0.1131 | 0.045* | 0.15 |
C133 | 0.0370 (10) | 0.5570 (8) | 0.119 (3) | 0.039 (2) | 0.15 |
H133 | −0.0041 | 0.6015 | 0.1084 | 0.047* | 0.15 |
C134 | 0.1204 (10) | 0.5783 (7) | 0.133 (7) | 0.039 (2) | 0.15 |
H134 | 0.1376 | 0.6375 | 0.1362 | 0.047* | 0.15 |
C135 | 0.1779 (9) | 0.5125 (8) | 0.143 (9) | 0.0365 (15) | 0.15 |
H135 | 0.2355 | 0.5274 | 0.1528 | 0.044* | 0.15 |
N105 | 0.2616 (8) | 0.1719 (7) | 0.125 (4) | 0.0268 (10) | 0.15 |
N106 | 0.1221 (7) | 0.2607 (6) | 0.124 (3) | 0.0267 (10) | 0.15 |
N107 | 0.1569 (7) | 0.4278 (7) | 0.139 (6) | 0.0282 (16) | 0.15 |
C128 | −0.036 (3) | 0.185 (3) | 0.127 (3) | 0.029 (3)* | 0.15 |
C136 | −0.2565 (12) | 0.1536 (15) | 0.1642 (14) | 0.029 (3)* | 0.15 |
H136 | −0.2954 | 0.1803 | 0.1935 | 0.035* | 0.15 |
C137 | −0.1765 (13) | 0.1876 (13) | 0.1695 (14) | 0.029 (3)* | 0.15 |
H137 | −0.1607 | 0.2374 | 0.2023 | 0.035* | 0.15 |
C138 | −0.1195 (10) | 0.1486 (15) | 0.1266 (15) | 0.029 (3)* | 0.15 |
C139 | −0.1425 (12) | 0.0756 (14) | 0.0785 (14) | 0.029 (3)* | 0.15 |
H139 | −0.1036 | 0.0490 | 0.0492 | 0.035* | 0.15 |
C140 | −0.2226 (13) | 0.0417 (13) | 0.0732 (14) | 0.029 (3)* | 0.15 |
H140 | −0.2384 | −0.0082 | 0.0403 | 0.035* | 0.15 |
N108 | −0.2796 (11) | 0.0807 (16) | 0.1160 (16) | 0.039 (13)* | 0.15 |
P1A | 0.42327 (11) | 0.62842 (12) | 0.19001 (12) | 0.0535 (5) | 0.6667 |
F1A | 0.3907 (5) | 0.5541 (6) | 0.2411 (5) | 0.0670 (5)* | 0.6667 |
F2A | 0.3333 (4) | 0.6356 (5) | 0.1268 (4) | 0.0670 (5)* | 0.6667 |
F3A | 0.4501 (4) | 0.7046 (4) | 0.1273 (4) | 0.0670 (5)* | 0.6667 |
F4A | 0.5117 (4) | 0.6332 (5) | 0.2411 (4) | 0.0670 (5)* | 0.6667 |
F5A | 0.4558 (4) | 0.5636 (5) | 0.1279 (5) | 0.0670 (5)* | 0.6667 |
F6A | 0.3903 (4) | 0.7023 (5) | 0.2432 (4) | 0.0670 (5)* | 0.6667 |
P1B | 0.42327 (11) | 0.62842 (12) | 0.19001 (12) | 0.0535 (5) | 0.3333 |
F1B | 0.3743 (9) | 0.5529 (11) | 0.2303 (10) | 0.0670 (5)* | 0.3333 |
F2B | 0.3353 (7) | 0.6633 (9) | 0.1540 (8) | 0.0670 (5)* | 0.3333 |
F3B | 0.4753 (8) | 0.7007 (8) | 0.1577 (8) | 0.0670 (5)* | 0.3333 |
F4B | 0.5110 (7) | 0.5810 (9) | 0.2381 (8) | 0.0670 (5)* | 0.3333 |
F5B | 0.4312 (8) | 0.5591 (9) | 0.1211 (9) | 0.0670 (5)* | 0.3333 |
F6B | 0.4290 (9) | 0.6817 (9) | 0.2777 (9) | 0.0670 (5)* | 0.3333 |
P2A | 0.01085 (12) | 0.34258 (13) | 0.37053 (11) | 0.0515 (5) | 0.6667 |
F7A | −0.0799 (4) | 0.3052 (5) | 0.3288 (4) | 0.0670 (5)* | 0.6667 |
F8A | 0.0523 (6) | 0.2825 (6) | 0.3097 (6) | 0.0670 (5)* | 0.6667 |
F9A | 0.1001 (4) | 0.3682 (4) | 0.4138 (4) | 0.0670 (5)* | 0.6667 |
F10A | −0.0116 (4) | 0.4151 (5) | 0.4360 (4) | 0.0670 (5)* | 0.6667 |
F11A | −0.0065 (4) | 0.4169 (4) | 0.3052 (4) | 0.0670 (5)* | 0.6667 |
F12A | 0.0152 (4) | 0.2618 (5) | 0.4337 (5) | 0.0670 (5)* | 0.6667 |
P2B | 0.01085 (12) | 0.34258 (13) | 0.37053 (11) | 0.0515 (5) | 0.3333 |
F7B | −0.0657 (7) | 0.3666 (9) | 0.3129 (7) | 0.0670 (5)* | 0.3333 |
F8B | 0.0417 (11) | 0.2716 (10) | 0.3099 (11) | 0.0670 (5)* | 0.3333 |
F9B | 0.1034 (7) | 0.3303 (9) | 0.4304 (8) | 0.0670 (5)* | 0.3333 |
F10B | −0.0470 (9) | 0.3850 (9) | 0.4251 (9) | 0.0670 (5)* | 0.3333 |
F11B | 0.0566 (8) | 0.4202 (8) | 0.3231 (8) | 0.0670 (5)* | 0.3333 |
F12B | −0.0136 (8) | 0.2662 (9) | 0.4254 (9) | 0.0670 (5)* | 0.3333 |
O1W | 0.5185 (7) | 0.3890 (7) | 0.5830 (7) | 0.0411 (19)* | 0.4 |
O2W | 0.5228 (8) | 0.4277 (8) | 0.5626 (8) | 0.0411 (19)* | 0.35 |
O3W | 0.5531 (17) | 0.4242 (18) | 0.5175 (17) | 0.0411 (19)* | 0.15 |
O4W | 0.637 (3) | 0.350 (3) | 0.392 (3) | 0.0411 (19)* | 0.1 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0196 (4) | 0.0389 (5) | 0.0244 (4) | −0.0075 (3) | 0.0051 (3) | −0.0017 (3) |
C1 | 0.030 (3) | 0.046 (3) | 0.029 (3) | −0.003 (2) | 0.009 (2) | 0.000 (2) |
C2 | 0.036 (3) | 0.072 (4) | 0.018 (3) | 0.001 (3) | 0.009 (2) | 0.000 (3) |
C3 | 0.037 (3) | 0.070 (4) | 0.020 (3) | 0.003 (3) | 0.003 (2) | −0.007 (3) |
C4 | 0.025 (3) | 0.057 (4) | 0.028 (3) | −0.002 (3) | 0.002 (2) | 0.002 (3) |
C5 | 0.022 (2) | 0.027 (3) | 0.025 (3) | −0.001 (2) | 0.002 (2) | 0.000 (2) |
C6 | 0.022 (2) | 0.028 (3) | 0.022 (2) | −0.002 (2) | 0.004 (2) | 0.000 (2) |
C7 | 0.022 (2) | 0.038 (3) | 0.026 (3) | 0.000 (2) | 0.000 (2) | 0.002 (2) |
C8 | 0.020 (2) | 0.033 (3) | 0.032 (3) | 0.002 (2) | 0.004 (2) | 0.001 (2) |
C9 | 0.025 (3) | 0.035 (3) | 0.026 (3) | −0.006 (2) | 0.008 (2) | 0.001 (2) |
C10 | 0.023 (2) | 0.031 (3) | 0.023 (3) | −0.002 (2) | 0.004 (2) | −0.003 (2) |
C11 | 0.023 (3) | 0.044 (3) | 0.022 (3) | −0.006 (2) | 0.002 (2) | −0.002 (2) |
C12 | 0.026 (3) | 0.060 (4) | 0.027 (3) | −0.012 (3) | 0.008 (2) | −0.004 (3) |
C13 | 0.040 (3) | 0.066 (4) | 0.026 (3) | −0.008 (3) | 0.006 (3) | −0.002 (3) |
C14 | 0.030 (3) | 0.064 (4) | 0.027 (3) | −0.004 (3) | 0.000 (2) | −0.002 (3) |
C15 | 0.028 (3) | 0.054 (4) | 0.026 (3) | −0.012 (3) | 0.004 (2) | 0.002 (3) |
C16 | 0.023 (3) | 0.086 (5) | 0.047 (4) | 0.000 (3) | 0.001 (3) | 0.009 (4) |
C17 | 0.022 (3) | 0.088 (5) | 0.043 (4) | −0.003 (3) | 0.002 (3) | 0.011 (3) |
C18 | 0.020 (3) | 0.036 (3) | 0.039 (3) | 0.004 (2) | 0.007 (2) | 0.003 (2) |
C19 | 0.028 (3) | 0.074 (5) | 0.045 (4) | −0.002 (3) | 0.008 (3) | 0.004 (3) |
C20 | 0.036 (4) | 0.087 (5) | 0.054 (4) | −0.014 (4) | 0.020 (3) | −0.002 (4) |
N1 | 0.024 (2) | 0.033 (2) | 0.027 (2) | −0.0025 (18) | 0.0052 (18) | −0.0021 (19) |
N2 | 0.021 (2) | 0.034 (2) | 0.026 (2) | −0.0023 (18) | 0.0061 (17) | 0.0006 (18) |
N3 | 0.021 (2) | 0.040 (3) | 0.025 (2) | −0.0082 (19) | 0.0018 (17) | −0.0023 (19) |
N4 | 0.022 (2) | 0.069 (4) | 0.054 (3) | 0.000 (2) | 0.005 (2) | 0.000 (3) |
C21 | 0.023 (3) | 0.042 (3) | 0.024 (3) | 0.000 (3) | −0.001 (4) | 0.006 (2) |
C22 | 0.033 (4) | 0.044 (4) | 0.041 (4) | 0.005 (3) | 0.002 (5) | 0.006 (3) |
C23 | 0.041 (5) | 0.036 (4) | 0.071 (5) | −0.003 (3) | −0.002 (5) | 0.004 (3) |
C24 | 0.027 (4) | 0.050 (4) | 0.056 (4) | −0.007 (3) | 0.002 (5) | 0.002 (4) |
C25 | 0.022 (3) | 0.038 (3) | 0.029 (3) | −0.010 (2) | 0.002 (3) | 0.000 (3) |
C26 | 0.024 (3) | 0.045 (4) | 0.024 (3) | −0.012 (3) | 0.004 (3) | −0.002 (3) |
C27 | 0.026 (3) | 0.043 (4) | 0.032 (5) | −0.009 (3) | 0.007 (3) | −0.001 (3) |
C29 | 0.019 (3) | 0.048 (4) | 0.034 (5) | −0.004 (3) | 0.006 (3) | −0.008 (3) |
C30 | 0.019 (3) | 0.042 (3) | 0.028 (3) | −0.006 (2) | 0.007 (3) | −0.005 (3) |
C31 | 0.018 (2) | 0.045 (3) | 0.023 (3) | −0.002 (2) | 0.004 (2) | −0.002 (3) |
C32 | 0.022 (3) | 0.047 (4) | 0.043 (5) | −0.005 (3) | 0.009 (3) | −0.012 (4) |
C33 | 0.029 (3) | 0.050 (4) | 0.038 (5) | 0.002 (3) | 0.005 (3) | −0.012 (3) |
C34 | 0.041 (3) | 0.034 (3) | 0.042 (7) | −0.009 (3) | 0.005 (3) | −0.010 (4) |
C35 | 0.027 (3) | 0.045 (4) | 0.040 (4) | −0.005 (3) | 0.011 (3) | −0.002 (4) |
N5 | 0.024 (3) | 0.035 (3) | 0.022 (2) | −0.003 (2) | 0.004 (3) | −0.001 (2) |
N6 | 0.018 (2) | 0.036 (3) | 0.027 (2) | −0.005 (2) | 0.006 (2) | −0.002 (2) |
N7 | 0.018 (2) | 0.039 (3) | 0.028 (5) | −0.0029 (19) | 0.005 (2) | −0.002 (3) |
C28 | 0.023 (3) | 0.038 (4) | 0.028 (4) | −0.007 (3) | 0.007 (3) | 0.001 (3) |
C36 | 0.040 (5) | 0.064 (6) | 0.061 (6) | −0.015 (4) | 0.012 (4) | 0.012 (4) |
C37 | 0.025 (3) | 0.052 (4) | 0.054 (4) | −0.010 (3) | 0.004 (3) | 0.005 (4) |
C38 | 0.024 (3) | 0.047 (4) | 0.038 (4) | −0.010 (3) | 0.006 (3) | −0.007 (3) |
C39 | 0.031 (4) | 0.052 (4) | 0.045 (4) | −0.010 (3) | 0.006 (3) | −0.006 (3) |
C40 | 0.026 (3) | 0.058 (5) | 0.050 (4) | −0.003 (3) | −0.001 (3) | −0.014 (4) |
N8 | 0.027 (3) | 0.057 (4) | 0.067 (4) | −0.011 (3) | 0.008 (3) | −0.004 (4) |
C121 | 0.023 (3) | 0.042 (3) | 0.024 (3) | 0.000 (3) | −0.001 (4) | 0.006 (2) |
C122 | 0.033 (4) | 0.044 (4) | 0.041 (4) | 0.005 (3) | 0.002 (5) | 0.006 (3) |
C123 | 0.041 (5) | 0.036 (4) | 0.071 (5) | −0.003 (3) | −0.002 (5) | 0.004 (3) |
C124 | 0.027 (4) | 0.050 (4) | 0.056 (4) | −0.007 (3) | 0.002 (5) | 0.002 (4) |
C125 | 0.022 (3) | 0.038 (3) | 0.029 (3) | −0.010 (2) | 0.002 (3) | 0.000 (3) |
C126 | 0.024 (3) | 0.045 (4) | 0.024 (3) | −0.012 (3) | 0.004 (3) | −0.002 (3) |
C127 | 0.026 (3) | 0.043 (4) | 0.032 (5) | −0.009 (3) | 0.007 (3) | −0.001 (3) |
C129 | 0.019 (3) | 0.048 (4) | 0.034 (5) | −0.004 (3) | 0.006 (3) | −0.008 (3) |
C130 | 0.019 (3) | 0.042 (3) | 0.028 (3) | −0.006 (2) | 0.007 (3) | −0.005 (3) |
C131 | 0.018 (2) | 0.045 (3) | 0.023 (3) | −0.002 (2) | 0.004 (2) | −0.002 (3) |
C132 | 0.022 (3) | 0.047 (4) | 0.043 (5) | −0.005 (3) | 0.009 (3) | −0.012 (4) |
C133 | 0.029 (3) | 0.050 (4) | 0.038 (5) | 0.002 (3) | 0.005 (3) | −0.012 (3) |
C134 | 0.041 (3) | 0.034 (3) | 0.042 (7) | −0.009 (3) | 0.005 (3) | −0.010 (4) |
C135 | 0.027 (3) | 0.045 (4) | 0.040 (4) | −0.005 (3) | 0.011 (3) | −0.002 (4) |
N105 | 0.024 (3) | 0.035 (3) | 0.022 (2) | −0.003 (2) | 0.004 (3) | −0.001 (2) |
N106 | 0.018 (2) | 0.036 (3) | 0.027 (2) | −0.005 (2) | 0.006 (2) | −0.002 (2) |
N107 | 0.018 (2) | 0.039 (3) | 0.028 (5) | −0.0029 (19) | 0.005 (2) | −0.002 (3) |
P1A | 0.0462 (10) | 0.0529 (11) | 0.0672 (12) | −0.0157 (8) | 0.0263 (9) | −0.0193 (9) |
P1B | 0.0462 (10) | 0.0529 (11) | 0.0672 (12) | −0.0157 (8) | 0.0263 (9) | −0.0193 (9) |
P2A | 0.0512 (10) | 0.0674 (12) | 0.0375 (9) | 0.0224 (9) | 0.0124 (8) | 0.0119 (8) |
P2B | 0.0512 (10) | 0.0674 (12) | 0.0375 (9) | 0.0224 (9) | 0.0124 (8) | 0.0119 (8) |
Mn1—N1 | 2.231 (4) | C28—C38 | 1.496 (9) |
Mn1—N2 | 2.193 (4) | C36—N8 | 1.328 (11) |
Mn1—N3 | 2.268 (4) | C36—C37 | 1.402 (12) |
Mn1—N5 | 2.259 (5) | C36—H36 | 0.9500 |
Mn1—N6 | 2.212 (4) | C37—C38 | 1.373 (10) |
Mn1—N7 | 2.260 (5) | C37—H37 | 0.9500 |
Mn1—N105 | 2.373 (11) | C38—C39 | 1.394 (10) |
Mn1—N106 | 2.107 (10) | C39—C40 | 1.384 (9) |
Mn1—N107 | 2.090 (16) | C39—H39 | 0.9500 |
C1—N1 | 1.343 (7) | C40—N8 | 1.336 (10) |
C1—C2 | 1.371 (8) | C40—H40 | 0.9500 |
C1—H1 | 0.9500 | C121—N105 | 1.336 (7) |
C2—C3 | 1.387 (8) | C121—C122 | 1.372 (8) |
C2—H2 | 0.9500 | C121—H121 | 0.9500 |
C3—C4 | 1.374 (8) | C122—C123 | 1.377 (9) |
C3—H3 | 0.9500 | C122—H122 | 0.9500 |
C4—C5 | 1.388 (7) | C123—C124 | 1.377 (9) |
C4—H4 | 0.9500 | C123—H123 | 0.9500 |
C5—N1 | 1.352 (6) | C124—C125 | 1.380 (9) |
C5—C6 | 1.484 (7) | C124—H124 | 0.9500 |
C6—N2 | 1.338 (6) | C125—N105 | 1.356 (7) |
C6—C7 | 1.388 (7) | C125—C126 | 1.481 (8) |
C7—C8 | 1.388 (7) | C126—N106 | 1.348 (7) |
C7—H7 | 0.9500 | C126—C127 | 1.382 (7) |
C8—C9 | 1.393 (7) | C127—C128 | 1.40 (5) |
C8—C18 | 1.487 (7) | C127—H127 | 0.9500 |
C9—C10 | 1.380 (7) | C129—C130 | 1.391 (7) |
C9—H9 | 0.9500 | C129—C128 | 1.47 (5) |
C10—N2 | 1.343 (6) | C129—H129 | 0.9500 |
C10—C11 | 1.489 (7) | C130—N106 | 1.336 (7) |
C11—N3 | 1.346 (6) | C130—C131 | 1.478 (8) |
C11—C12 | 1.389 (7) | C131—N107 | 1.351 (6) |
C12—C13 | 1.378 (8) | C131—C132 | 1.391 (8) |
C12—H12 | 0.9500 | C132—C133 | 1.374 (9) |
C13—C14 | 1.385 (8) | C132—H132 | 0.9500 |
C13—H13 | 0.9500 | C133—C134 | 1.375 (8) |
C14—C15 | 1.393 (8) | C133—H133 | 0.9500 |
C14—H14 | 0.9500 | C134—C135 | 1.368 (9) |
C15—N3 | 1.334 (7) | C134—H134 | 0.9500 |
C15—H15 | 0.9500 | C135—N107 | 1.343 (7) |
C16—N4 | 1.315 (8) | C135—H135 | 0.9500 |
C16—C17 | 1.381 (8) | C128—C138 | 1.46 (5) |
C16—H16 | 0.9500 | C136—C137 | 1.3900 |
C17—C18 | 1.380 (8) | C136—N108 | 1.3900 |
C17—H17 | 0.9500 | C136—H136 | 0.9500 |
C18—C19 | 1.376 (8) | C137—C138 | 1.3900 |
C19—C20 | 1.393 (8) | C137—H137 | 0.9500 |
C19—H19 | 0.9500 | C138—C139 | 1.3900 |
C20—N4 | 1.322 (9) | C139—C140 | 1.3900 |
C20—H20 | 0.9500 | C139—H139 | 0.9500 |
C21—N5 | 1.336 (7) | C140—N108 | 1.3900 |
C21—C22 | 1.372 (8) | C140—H140 | 0.9500 |
C21—H21 | 0.9500 | P1A—F4A | 1.544 (6) |
C22—C23 | 1.377 (9) | P1A—F1A | 1.564 (7) |
C22—H22 | 0.9500 | P1A—F5A | 1.582 (7) |
C23—C24 | 1.377 (9) | P1A—F6A | 1.583 (7) |
C23—H23 | 0.9500 | P1A—F2A | 1.656 (7) |
C24—C25 | 1.380 (9) | P1A—F3A | 1.669 (7) |
C24—H24 | 0.9500 | P1B—F3B | 1.542 (11) |
C25—N5 | 1.356 (6) | P1B—F2B | 1.550 (11) |
C25—C26 | 1.481 (8) | P1B—F5B | 1.581 (11) |
C26—N6 | 1.348 (7) | P1B—F1B | 1.611 (11) |
C26—C27 | 1.382 (7) | P1B—F6B | 1.656 (14) |
C27—C28 | 1.391 (10) | P1B—F4B | 1.679 (11) |
C27—H27 | 0.9500 | P2A—F9A | 1.558 (7) |
C29—C28 | 1.386 (10) | P2A—F11A | 1.565 (6) |
C29—C30 | 1.391 (7) | P2A—F8A | 1.593 (7) |
C29—H29 | 0.9500 | P2A—F12A | 1.616 (7) |
C30—N6 | 1.336 (7) | P2A—F7A | 1.627 (7) |
C30—C31 | 1.477 (8) | P2A—F10A | 1.636 (7) |
C31—N7 | 1.351 (6) | P2B—F7B | 1.484 (11) |
C31—C32 | 1.391 (8) | P2B—F10B | 1.549 (14) |
C32—C33 | 1.374 (9) | P2B—F12B | 1.573 (11) |
C32—H32 | 0.9500 | P2B—F8B | 1.615 (12) |
C33—C34 | 1.375 (8) | P2B—F11B | 1.668 (11) |
C33—H33 | 0.9500 | P2B—F9B | 1.670 (11) |
C34—C35 | 1.368 (9) | O1W—O2W | 0.693 (13) |
C34—H34 | 0.9500 | O1W—O3W | 1.41 (3) |
C35—N7 | 1.343 (7) | O2W—O3W | 0.96 (3) |
C35—H35 | 0.9500 | ||
N1—Mn1—N2 | 72.37 (15) | C29—C28—C38 | 118.6 (6) |
N1—Mn1—N3 | 143.36 (15) | C27—C28—C38 | 122.3 (6) |
N1—Mn1—N5 | 99.8 (3) | N8—C36—C37 | 124.3 (9) |
N1—Mn1—N6 | 111.3 (3) | N8—C36—H36 | 117.9 |
N1—Mn1—N7 | 92.2 (4) | C37—C36—H36 | 117.9 |
N2—Mn1—N3 | 72.21 (15) | C38—C37—C36 | 118.0 (7) |
N2—Mn1—N5 | 97.87 (16) | C38—C37—H37 | 121.0 |
N2—Mn1—N6 | 169.95 (18) | C36—C37—H37 | 121.0 |
N2—Mn1—N7 | 117.68 (17) | C37—C38—C39 | 118.7 (6) |
N3—Mn1—N5 | 94.0 (3) | C37—C38—C28 | 121.9 (7) |
N3—Mn1—N6 | 105.2 (3) | C39—C38—C28 | 119.4 (6) |
N3—Mn1—N7 | 96.0 (4) | C40—C39—C38 | 118.5 (7) |
N5—Mn1—N6 | 72.45 (17) | C40—C39—H39 | 120.7 |
N5—Mn1—N7 | 144.44 (17) | C38—C39—H39 | 120.7 |
N6—Mn1—N7 | 71.99 (17) | N8—C40—C39 | 123.9 (7) |
N107—Mn1—N106 | 77.6 (5) | N8—C40—H40 | 118.1 |
N107—Mn1—N2 | 118.8 (4) | C39—C40—H40 | 118.1 |
N106—Mn1—N2 | 163.6 (3) | C36—N8—C40 | 116.5 (7) |
N107—Mn1—N1 | 89 (2) | N105—C121—C122 | 123.4 (6) |
N106—Mn1—N1 | 110.1 (14) | N105—C121—H121 | 118.3 |
N107—Mn1—N3 | 100 (3) | C122—C121—H121 | 118.3 |
N106—Mn1—N3 | 106.5 (14) | C121—C122—C123 | 118.0 (6) |
N107—Mn1—N105 | 149.2 (10) | C121—C122—H122 | 121.0 |
N106—Mn1—N105 | 72.0 (3) | C123—C122—H122 | 121.0 |
N2—Mn1—N105 | 91.6 (3) | C122—C123—C124 | 119.6 (7) |
N1—Mn1—N105 | 96.8 (16) | C122—C123—H123 | 120.2 |
N3—Mn1—N105 | 93.3 (17) | C124—C123—H123 | 120.2 |
N1—C1—C2 | 122.4 (5) | C123—C124—C125 | 119.6 (6) |
N1—C1—H1 | 118.8 | C123—C124—H124 | 120.2 |
C2—C1—H1 | 118.8 | C125—C124—H124 | 120.2 |
C1—C2—C3 | 118.8 (5) | N105—C125—C124 | 120.7 (6) |
C1—C2—H2 | 120.6 | N105—C125—C126 | 116.0 (5) |
C3—C2—H2 | 120.6 | C124—C125—C126 | 123.2 (5) |
C4—C3—C2 | 119.2 (5) | N106—C126—C127 | 120.5 (6) |
C4—C3—H3 | 120.4 | N106—C126—C125 | 114.9 (5) |
C2—C3—H3 | 120.4 | C127—C126—C125 | 124.5 (6) |
C3—C4—C5 | 119.5 (5) | C126—C127—C128 | 123 (2) |
C3—C4—H4 | 120.3 | C126—C127—H127 | 118.4 |
C5—C4—H4 | 120.3 | C128—C127—H127 | 118.4 |
N1—C5—C4 | 121.0 (5) | C130—C129—C128 | 120.8 (19) |
N1—C5—C6 | 114.9 (4) | C130—C129—H129 | 119.6 |
C4—C5—C6 | 124.1 (4) | C128—C129—H129 | 119.6 |
N2—C6—C7 | 121.0 (4) | N106—C130—C129 | 121.0 (6) |
N2—C6—C5 | 114.7 (4) | N106—C130—C131 | 115.7 (4) |
C7—C6—C5 | 124.2 (4) | C129—C130—C131 | 123.2 (6) |
C8—C7—C6 | 119.9 (5) | N107—C131—C132 | 121.7 (5) |
C8—C7—H7 | 120.1 | N107—C131—C130 | 115.0 (5) |
C6—C7—H7 | 120.1 | C132—C131—C130 | 123.2 (5) |
C7—C8—C9 | 118.2 (5) | C133—C132—C131 | 118.8 (5) |
C7—C8—C18 | 121.8 (5) | C133—C132—H132 | 120.6 |
C9—C8—C18 | 120.0 (5) | C131—C132—H132 | 120.6 |
C10—C9—C8 | 119.3 (5) | C132—C133—C134 | 119.7 (6) |
C10—C9—H9 | 120.4 | C132—C133—H133 | 120.2 |
C8—C9—H9 | 120.4 | C134—C133—H133 | 120.2 |
N2—C10—C9 | 121.8 (5) | C135—C134—C133 | 118.6 (6) |
N2—C10—C11 | 114.1 (4) | C135—C134—H134 | 120.7 |
C9—C10—C11 | 124.0 (5) | C133—C134—H134 | 120.7 |
N3—C11—C12 | 121.4 (5) | N107—C135—C134 | 123.1 (6) |
N3—C11—C10 | 115.9 (4) | N107—C135—H135 | 118.5 |
C12—C11—C10 | 122.7 (5) | C134—C135—H135 | 118.5 |
C13—C12—C11 | 118.9 (5) | C121—N105—C125 | 118.6 (5) |
C13—C12—H12 | 120.6 | C121—N105—Mn1 | 128.0 (5) |
C11—C12—H12 | 120.6 | C125—N105—Mn1 | 113.4 (4) |
C12—C13—C14 | 119.9 (5) | C130—N106—C126 | 120.8 (5) |
C12—C13—H13 | 120.0 | C130—N106—Mn1 | 115.5 (5) |
C14—C13—H13 | 120.0 | C126—N106—Mn1 | 123.7 (5) |
C13—C14—C15 | 118.0 (5) | C135—N107—C131 | 118.0 (5) |
C13—C14—H14 | 121.0 | C135—N107—Mn1 | 125.5 (13) |
C15—C14—H14 | 121.0 | C131—N107—Mn1 | 115.6 (6) |
N3—C15—C14 | 122.3 (5) | C127—C128—C138 | 125 (3) |
N3—C15—H15 | 118.8 | C127—C128—C129 | 114 (3) |
C14—C15—H15 | 118.8 | C138—C128—C129 | 121 (3) |
N4—C16—C17 | 124.0 (6) | C137—C136—N108 | 120.0 |
N4—C16—H16 | 118.0 | C137—C136—H136 | 120.0 |
C17—C16—H16 | 118.0 | N108—C136—H136 | 120.0 |
C18—C17—C16 | 120.1 (6) | C136—C137—C138 | 120.0 |
C18—C17—H17 | 119.9 | C136—C137—H137 | 120.0 |
C16—C17—H17 | 119.9 | C138—C137—H137 | 120.0 |
C19—C18—C17 | 115.9 (5) | C139—C138—C137 | 120.0 |
C19—C18—C8 | 121.3 (5) | C139—C138—C128 | 118 (2) |
C17—C18—C8 | 122.5 (5) | C137—C138—C128 | 122 (2) |
C18—C19—C20 | 120.0 (6) | C140—C139—C138 | 120.0 |
C18—C19—H19 | 120.0 | C140—C139—H139 | 120.0 |
C20—C19—H19 | 120.0 | C138—C139—H139 | 120.0 |
N4—C20—C19 | 123.5 (6) | C139—C140—N108 | 120.0 |
N4—C20—H20 | 118.3 | C139—C140—H140 | 120.0 |
C19—C20—H20 | 118.3 | N108—C140—H140 | 120.0 |
C1—N1—C5 | 119.0 (4) | C140—N108—C136 | 120.0 |
C1—N1—Mn1 | 123.2 (4) | F4A—P1A—F1A | 96.0 (4) |
C5—N1—Mn1 | 117.7 (3) | F4A—P1A—F5A | 90.4 (4) |
C6—N2—C10 | 119.9 (4) | F1A—P1A—F5A | 94.1 (5) |
C6—N2—Mn1 | 119.6 (3) | F4A—P1A—F6A | 91.7 (4) |
C10—N2—Mn1 | 120.2 (3) | F1A—P1A—F6A | 92.7 (5) |
C15—N3—C11 | 119.4 (4) | F5A—P1A—F6A | 172.7 (4) |
C15—N3—Mn1 | 123.8 (3) | F4A—P1A—F2A | 171.2 (4) |
C11—N3—Mn1 | 116.8 (3) | F1A—P1A—F2A | 92.8 (4) |
C16—N4—C20 | 116.4 (5) | F5A—P1A—F2A | 89.2 (4) |
N5—C21—C22 | 123.4 (5) | F6A—P1A—F2A | 87.7 (4) |
N5—C21—H21 | 118.3 | F4A—P1A—F3A | 89.6 (4) |
C22—C21—H21 | 118.3 | F1A—P1A—F3A | 173.9 (4) |
C21—C22—C23 | 118.0 (6) | F5A—P1A—F3A | 83.5 (4) |
C21—C22—H22 | 121.0 | F6A—P1A—F3A | 89.5 (4) |
C23—C22—H22 | 121.0 | F2A—P1A—F3A | 81.5 (3) |
C22—C23—C24 | 119.6 (6) | F3B—P1B—F2B | 98.1 (7) |
C22—C23—H23 | 120.2 | F3B—P1B—F5B | 96.9 (7) |
C24—C23—H23 | 120.2 | F2B—P1B—F5B | 97.7 (7) |
C23—C24—C25 | 119.7 (6) | F3B—P1B—F1B | 175.5 (8) |
C23—C24—H24 | 120.2 | F2B—P1B—F1B | 85.5 (7) |
C25—C24—H24 | 120.2 | F5B—P1B—F1B | 85.3 (9) |
N5—C25—C24 | 120.8 (5) | F3B—P1B—F6B | 89.6 (7) |
N5—C25—C26 | 116.0 (5) | F2B—P1B—F6B | 94.7 (7) |
C24—C25—C26 | 123.2 (5) | F5B—P1B—F6B | 165.0 (8) |
N6—C26—C27 | 120.5 (6) | F1B—P1B—F6B | 87.3 (9) |
N6—C26—C25 | 114.9 (4) | F3B—P1B—F4B | 90.3 (7) |
C27—C26—C25 | 124.5 (5) | F2B—P1B—F4B | 171.3 (7) |
C26—C27—C28 | 119.4 (6) | F5B—P1B—F4B | 83.5 (7) |
C26—C27—H27 | 120.3 | F1B—P1B—F4B | 86.0 (7) |
C28—C27—H27 | 120.3 | F6B—P1B—F4B | 82.9 (7) |
C28—C29—C30 | 118.9 (6) | F9A—P2A—F11A | 100.5 (4) |
C28—C29—H29 | 120.5 | F9A—P2A—F8A | 88.8 (4) |
C30—C29—H29 | 120.5 | F11A—P2A—F8A | 91.9 (4) |
N6—C30—C29 | 121.1 (5) | F9A—P2A—F12A | 87.5 (4) |
N6—C30—C31 | 115.7 (4) | F11A—P2A—F12A | 171.9 (4) |
C29—C30—C31 | 123.2 (5) | F8A—P2A—F12A | 89.2 (4) |
N7—C31—C32 | 121.7 (5) | F9A—P2A—F7A | 173.8 (4) |
N7—C31—C30 | 115.0 (5) | F11A—P2A—F7A | 85.1 (4) |
C32—C31—C30 | 123.2 (5) | F8A—P2A—F7A | 88.5 (4) |
C33—C32—C31 | 118.8 (5) | F12A—P2A—F7A | 86.9 (4) |
C33—C32—H32 | 120.6 | F9A—P2A—F10A | 79.3 (4) |
C31—C32—H32 | 120.6 | F11A—P2A—F10A | 85.8 (4) |
C32—C33—C34 | 119.7 (6) | F8A—P2A—F10A | 167.3 (4) |
C32—C33—H33 | 120.1 | F12A—P2A—F10A | 94.8 (4) |
C34—C33—H33 | 120.1 | F7A—P2A—F10A | 103.7 (4) |
C35—C34—C33 | 118.7 (6) | F7B—P2B—F10B | 75.3 (7) |
C35—C34—H34 | 120.7 | F7B—P2B—F12B | 107.1 (7) |
C33—C34—H34 | 120.7 | F10B—P2B—F12B | 75.1 (8) |
N7—C35—C34 | 123.1 (5) | F7B—P2B—F8B | 94.6 (9) |
N7—C35—H35 | 118.4 | F10B—P2B—F8B | 157.7 (8) |
C34—C35—H35 | 118.4 | F12B—P2B—F8B | 89.4 (8) |
C21—N5—C25 | 118.6 (5) | F7B—P2B—F11B | 84.9 (7) |
C21—N5—Mn1 | 124.3 (4) | F10B—P2B—F11B | 109.5 (7) |
C25—N5—Mn1 | 117.1 (4) | F12B—P2B—F11B | 168.1 (7) |
C30—N6—C26 | 120.8 (4) | F8B—P2B—F11B | 89.0 (7) |
C30—N6—Mn1 | 119.5 (3) | F7B—P2B—F9B | 170.8 (7) |
C26—N6—Mn1 | 119.6 (4) | F10B—P2B—F9B | 105.9 (7) |
C35—N7—C31 | 118.0 (5) | F12B—P2B—F9B | 82.0 (6) |
C35—N7—Mn1 | 124.3 (4) | F8B—P2B—F9B | 87.3 (8) |
C31—N7—Mn1 | 117.6 (4) | F11B—P2B—F9B | 86.1 (7) |
C29—C28—C27 | 119.1 (6) | O1W—O2W—O3W | 116 (3) |
N1—C1—C2—C3 | −1.5 (10) | C31—C30—N6—C26 | 178.8 (8) |
C1—C2—C3—C4 | 1.1 (10) | C29—C30—N6—Mn1 | 173.7 (7) |
C2—C3—C4—C5 | 0.1 (10) | C31—C30—N6—Mn1 | −5.2 (9) |
C3—C4—C5—N1 | −1.1 (9) | C27—C26—N6—C30 | −0.7 (12) |
C3—C4—C5—C6 | 177.0 (5) | C25—C26—N6—C30 | 177.3 (7) |
N1—C5—C6—N2 | 2.3 (7) | C27—C26—N6—Mn1 | −176.8 (7) |
C4—C5—C6—N2 | −175.9 (5) | C25—C26—N6—Mn1 | 1.3 (10) |
N1—C5—C6—C7 | 179.3 (5) | C34—C35—N7—C31 | 0 (2) |
C4—C5—C6—C7 | 1.1 (8) | C34—C35—N7—Mn1 | −177.4 (15) |
N2—C6—C7—C8 | −0.7 (8) | C32—C31—N7—C35 | −1.0 (15) |
C5—C6—C7—C8 | −177.5 (5) | C30—C31—N7—C35 | −178.2 (12) |
C6—C7—C8—C9 | −0.3 (8) | C32—C31—N7—Mn1 | 177.0 (9) |
C6—C7—C8—C18 | 178.3 (5) | C30—C31—N7—Mn1 | −0.3 (10) |
C7—C8—C9—C10 | 1.2 (8) | C30—C29—C28—C27 | 0.4 (10) |
C18—C8—C9—C10 | −177.5 (5) | C30—C29—C28—C38 | −179.3 (7) |
C8—C9—C10—N2 | −1.2 (8) | C26—C27—C28—C29 | −3.3 (11) |
C8—C9—C10—C11 | 175.0 (5) | C26—C27—C28—C38 | 176.4 (7) |
N2—C10—C11—N3 | −5.8 (7) | N8—C36—C37—C38 | 1.3 (13) |
C9—C10—C11—N3 | 177.8 (5) | C36—C37—C38—C39 | −1.7 (11) |
N2—C10—C11—C12 | 172.5 (5) | C36—C37—C38—C28 | 176.3 (7) |
C9—C10—C11—C12 | −3.9 (9) | C29—C28—C38—C37 | −135.8 (8) |
N3—C11—C12—C13 | 1.9 (9) | C27—C28—C38—C37 | 44.4 (10) |
C10—C11—C12—C13 | −176.3 (6) | C29—C28—C38—C39 | 42.1 (9) |
C11—C12—C13—C14 | −2.0 (10) | C27—C28—C38—C39 | −137.6 (7) |
C12—C13—C14—C15 | 0.7 (10) | C37—C38—C39—C40 | 0.4 (11) |
C13—C14—C15—N3 | 0.6 (10) | C28—C38—C39—C40 | −177.6 (6) |
N4—C16—C17—C18 | −1.4 (12) | C38—C39—C40—N8 | 1.6 (11) |
C16—C17—C18—C19 | −1.5 (10) | C37—C36—N8—C40 | 0.5 (13) |
C16—C17—C18—C8 | −176.6 (6) | C39—C40—N8—C36 | −1.9 (12) |
C7—C8—C18—C19 | −155.2 (6) | N105—C121—C122—C123 | 1 (11) |
C9—C8—C18—C19 | 23.4 (8) | C121—C122—C123—C124 | −3 (8) |
C7—C8—C18—C17 | 19.7 (9) | C122—C123—C124—C125 | 2 (9) |
C9—C8—C18—C17 | −161.7 (6) | C123—C124—C125—N105 | 1 (8) |
C17—C18—C19—C20 | 2.1 (10) | C123—C124—C125—C126 | 179 (6) |
C8—C18—C19—C20 | 177.3 (6) | N105—C125—C126—N106 | 2 (5) |
C18—C19—C20—N4 | 0.1 (12) | C124—C125—C126—N106 | −175 (5) |
C2—C1—N1—C5 | 0.6 (8) | N105—C125—C126—C127 | −175 (5) |
C2—C1—N1—Mn1 | 178.4 (5) | C124—C125—C126—C127 | 7 (6) |
C4—C5—N1—C1 | 0.8 (8) | N106—C126—C127—C128 | 3 (7) |
C6—C5—N1—C1 | −177.5 (5) | C125—C126—C127—C128 | −180 (4) |
C4—C5—N1—Mn1 | −177.2 (4) | C128—C129—C130—N106 | 0 (6) |
C6—C5—N1—Mn1 | 4.5 (6) | C128—C129—C130—C131 | −176 (4) |
C7—C6—N2—C10 | 0.7 (8) | N106—C130—C131—N107 | −5 (4) |
C5—C6—N2—C10 | 177.8 (5) | C129—C130—C131—N107 | 171 (5) |
C7—C6—N2—Mn1 | 174.5 (4) | N106—C130—C131—C132 | 171 (5) |
C5—C6—N2—Mn1 | −8.3 (6) | C129—C130—C131—C132 | −13 (5) |
C9—C10—N2—C6 | 0.2 (8) | N107—C131—C132—C133 | 1 (7) |
C11—C10—N2—C6 | −176.3 (5) | C130—C131—C132—C133 | −175 (6) |
C9—C10—N2—Mn1 | −173.6 (4) | C131—C132—C133—C134 | −4 (6) |
C11—C10—N2—Mn1 | 9.9 (6) | C132—C133—C134—C135 | 4 (9) |
C14—C15—N3—C11 | −0.7 (9) | C133—C134—C135—N107 | 0 (13) |
C14—C15—N3—Mn1 | 177.6 (5) | C122—C121—N105—C125 | 2 (11) |
C12—C11—N3—C15 | −0.6 (9) | C122—C121—N105—Mn1 | −177 (6) |
C10—C11—N3—C15 | 177.7 (5) | C124—C125—N105—C121 | −3 (7) |
C12—C11—N3—Mn1 | −179.0 (5) | C126—C125—N105—C121 | 179 (5) |
C10—C11—N3—Mn1 | −0.6 (6) | C124—C125—N105—Mn1 | 176 (5) |
C17—C16—N4—C20 | 3.5 (12) | C126—C125—N105—Mn1 | −2 (5) |
C19—C20—N4—C16 | −2.9 (11) | C129—C130—N106—C126 | 2 (5) |
N5—C21—C22—C23 | −0.4 (18) | C131—C130—N106—C126 | 178 (4) |
C21—C22—C23—C24 | 0.0 (16) | C129—C130—N106—Mn1 | −177 (4) |
C22—C23—C24—C25 | 0.4 (16) | C131—C130—N106—Mn1 | −1 (4) |
C23—C24—C25—N5 | −0.5 (15) | C127—C126—N106—C130 | −3 (6) |
C23—C24—C25—C26 | 177.4 (10) | C125—C126—N106—C130 | 180 (3) |
N5—C25—C26—N6 | −0.8 (10) | C127—C126—N106—Mn1 | 176 (4) |
C24—C25—C26—N6 | −178.7 (9) | C125—C126—N106—Mn1 | −1 (5) |
N5—C25—C26—C27 | 177.2 (9) | C134—C135—N107—C131 | −3 (11) |
C24—C25—C26—C27 | −0.7 (12) | C134—C135—N107—Mn1 | 165 (9) |
N6—C26—C27—C28 | 3.6 (12) | C132—C131—N107—C135 | 3 (8) |
C25—C26—C27—C28 | −174.3 (7) | C130—C131—N107—C135 | 179 (6) |
C28—C29—C30—N6 | 2.5 (11) | C132—C131—N107—Mn1 | −167 (5) |
C28—C29—C30—C31 | −178.7 (7) | C130—C131—N107—Mn1 | 9 (5) |
N6—C30—C31—N7 | 3.5 (10) | C126—C127—C128—C138 | 177 (4) |
C29—C30—C31—N7 | −175.4 (9) | C126—C127—C128—C129 | −1 (7) |
N6—C30—C31—C32 | −173.7 (9) | C130—C129—C128—C127 | 0 (6) |
C29—C30—C31—C32 | 7.4 (13) | C130—C129—C128—C138 | −179 (4) |
N7—C31—C32—C33 | 0.9 (13) | N108—C136—C137—C138 | 0.0 |
C30—C31—C32—C33 | 177.9 (9) | C136—C137—C138—C139 | 0.0 |
C31—C32—C33—C34 | −0.3 (13) | C136—C137—C138—C128 | 177 (3) |
C32—C33—C34—C35 | −0.2 (16) | C127—C128—C138—C139 | −39 (5) |
C33—C34—C35—N7 | 0 (2) | C129—C128—C138—C139 | 140 (4) |
C22—C21—N5—C25 | 0.4 (17) | C127—C128—C138—C137 | 144 (4) |
C22—C21—N5—Mn1 | −177.3 (10) | C129—C128—C138—C137 | −37 (5) |
C24—C25—N5—C21 | 0.0 (14) | C137—C138—C139—C140 | 0.0 |
C26—C25—N5—C21 | −177.9 (9) | C128—C138—C139—C140 | −177 (3) |
C24—C25—N5—Mn1 | 177.9 (8) | C138—C139—C140—N108 | 0.0 |
C26—C25—N5—Mn1 | −0.1 (10) | C139—C140—N108—C136 | 0.0 |
C29—C30—N6—C26 | −2.3 (12) | C137—C136—N108—C140 | 0.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···F5Ai | 0.95 | 2.50 | 3.422 (9) | 164 |
C15—H15···F12Aii | 0.95 | 2.46 | 3.305 (9) | 149 |
C16—H16···F7Aiii | 0.95 | 2.38 | 3.289 (9) | 160 |
C19—H19···F5Ai | 0.95 | 2.41 | 3.328 (10) | 162 |
C29—H29···N4iv | 0.95 | 2.35 | 3.270 (8) | 163 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z−1/2; (iii) x+1, y, z; (iv) x−1, y, z. |
[Mn(C20H14N4)2](PF6)2·C3H6O | Dx = 1.595 Mg m−3 |
Mr = 1023.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, C2221 | Cell parameters from 6510 reflections |
a = 18.0996 (15) Å | θ = 2.7–25.2° |
b = 27.470 (2) Å | µ = 0.48 mm−1 |
c = 8.5734 (6) Å | T = 150 K |
V = 4262.7 (6) Å3 | Block, yellow |
Z = 4 | 0.16 × 0.08 × 0.04 mm |
F(000) = 2076 |
Bruker APEXII CCD diffractometer | 3908 independent reflections |
Radiation source: sealed tube | 2683 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
φ and ω scans | θmax = 25.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −21→21 |
Tmin = 0.955, Tmax = 0.981 | k = −31→33 |
18921 measured reflections | l = −10→10 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.104 | w = 1/[σ2(Fo2) + (0.0919P)2 + 48.9339P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.270 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.71 e Å−3 |
3908 reflections | Δρmin = −1.05 e Å−3 |
292 parameters | Absolute structure: Flack x determined using 836 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al. (2013) |
102 restraints | Absolute structure parameter: 0.21 (2) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Mn1 | 0.5000 | 0.77635 (9) | 0.7500 | 0.0370 (7) | |
C1 | 0.4292 (7) | 0.7832 (5) | 1.0872 (14) | 0.048 (3) | |
H1 | 0.4307 | 0.8172 | 1.0665 | 0.058* | |
C2 | 0.4020 (7) | 0.7676 (6) | 1.2295 (16) | 0.054 (4) | |
H2 | 0.3866 | 0.7902 | 1.3069 | 0.065* | |
C3 | 0.3980 (7) | 0.7181 (5) | 1.2545 (16) | 0.048 (3) | |
H3 | 0.3784 | 0.7062 | 1.3500 | 0.058* | |
C4 | 0.4219 (7) | 0.6858 (5) | 1.1433 (14) | 0.043 (3) | |
H4 | 0.4197 | 0.6517 | 1.1621 | 0.051* | |
C5 | 0.4488 (7) | 0.7032 (5) | 1.0052 (13) | 0.039 (3) | |
C6 | 0.4751 (6) | 0.6721 (4) | 0.8756 (12) | 0.032 (3) | |
C7 | 0.4750 (7) | 0.6216 (5) | 0.8755 (15) | 0.048 (3) | |
H7 | 0.4573 | 0.6046 | 0.9644 | 0.058* | |
C8 | 0.5000 | 0.5958 (6) | 0.7500 | 0.044 (4) | |
C12 | 0.3343 (7) | 0.7696 (6) | 0.6153 (14) | 0.050 (4) | |
H12 | 0.3387 | 0.7357 | 0.6366 | 0.060* | |
C13 | 0.2723 (8) | 0.7871 (6) | 0.5405 (16) | 0.056 (4) | |
H13 | 0.2342 | 0.7651 | 0.5120 | 0.068* | |
C14 | 0.2645 (8) | 0.8344 (7) | 0.5069 (18) | 0.061 (4) | |
H14 | 0.2217 | 0.8457 | 0.4539 | 0.073* | |
C15 | 0.3211 (7) | 0.8675 (6) | 0.5515 (17) | 0.054 (4) | |
H15 | 0.3180 | 0.9012 | 0.5279 | 0.064* | |
C16 | 0.3811 (7) | 0.8483 (5) | 0.6310 (14) | 0.040 (3) | |
C17 | 0.4424 (7) | 0.8814 (5) | 0.6884 (13) | 0.039 (3) | |
C18 | 0.4412 (7) | 0.9303 (5) | 0.6864 (14) | 0.041 (3) | |
H18 | 0.4002 | 0.9468 | 0.6417 | 0.049* | |
C19 | 0.5000 | 0.9574 (6) | 0.7500 | 0.046 (4) | |
C20 | 0.5000 | 1.0098 (7) | 0.7500 | 0.054 (5) | |
C21 | 0.4345 (8) | 1.0377 (5) | 0.7816 (19) | 0.058 (4) | |
H21 | 0.3892 | 1.0217 | 0.8040 | 0.069* | |
C22 | 0.4377 (9) | 1.0875 (5) | 0.779 (2) | 0.071 (5) | |
H22 | 0.3935 | 1.1051 | 0.7990 | 0.085* | |
N1 | 0.4541 (6) | 0.7520 (4) | 0.9758 (11) | 0.039 (3) | |
N2 | 0.5000 | 0.6970 (5) | 0.7500 | 0.035 (3) | |
N4 | 0.5000 | 0.8560 (5) | 0.7500 | 0.041 (3) | |
N5 | 0.3898 (6) | 0.8012 (4) | 0.6593 (11) | 0.039 (2) | |
N6 | 0.5000 | 1.1129 (5) | 0.7500 | 0.070 (5) | |
C109 | 0.5000 | 0.5411 (6) | 0.7500 | 0.049 (4) | 0.5 |
C110 | 0.4556 (18) | 0.5139 (11) | 0.646 (4) | 0.058 (6) | 0.5 |
H110 | 0.4251 | 0.5288 | 0.5695 | 0.070* | 0.5 |
C111 | 0.460 (2) | 0.4652 (12) | 0.663 (4) | 0.061 (6) | 0.5 |
H111 | 0.4270 | 0.4475 | 0.5977 | 0.074* | 0.5 |
N13 | 0.5000 | 0.4386 (6) | 0.7500 | 0.080 (6) | 0.5 |
C209 | 0.5000 | 0.5411 (6) | 0.7500 | 0.049 (4) | 0.5 |
C210 | 0.4316 (18) | 0.5177 (10) | 0.765 (4) | 0.058 (6) | 0.5 |
H210 | 0.3863 | 0.5347 | 0.7785 | 0.070* | 0.5 |
C211 | 0.436 (2) | 0.4708 (10) | 0.758 (4) | 0.061 (6) | 0.5 |
H211 | 0.3894 | 0.4545 | 0.7588 | 0.074* | 0.5 |
N23 | 0.5000 | 0.4386 (6) | 0.7500 | 0.080 (6) | 0.5 |
P1 | 0.7697 (4) | 0.8833 (3) | 0.4862 (10) | 0.0683 (16)* | 0.4 |
F11 | 0.7203 (7) | 0.8354 (4) | 0.4710 (17) | 0.0978 (19)* | 0.4 |
F12 | 0.7479 (8) | 0.8984 (5) | 0.3127 (13) | 0.0978 (19)* | 0.4 |
F13 | 0.8190 (7) | 0.9311 (4) | 0.5015 (17) | 0.0978 (19)* | 0.4 |
F14 | 0.7915 (8) | 0.8681 (5) | 0.6597 (13) | 0.0978 (19)* | 0.4 |
F15 | 0.8393 (7) | 0.8541 (5) | 0.4211 (17) | 0.0978 (19)* | 0.4 |
F16 | 0.7000 (7) | 0.9124 (5) | 0.5513 (17) | 0.0978 (19)* | 0.4 |
P2 | 0.7698 (5) | 0.8722 (3) | 0.4736 (11) | 0.0683 (16)* | 0.6 |
F21 | 0.7250 (10) | 0.8513 (7) | 0.330 (2) | 0.0978 (19)* | 0.6 |
F22 | 0.7976 (10) | 0.9225 (7) | 0.422 (2) | 0.0978 (19)* | 0.6 |
F23 | 0.8155 (10) | 0.8818 (7) | 0.635 (2) | 0.0978 (19)* | 0.6 |
F24 | 0.7524 (10) | 0.8204 (7) | 0.557 (2) | 0.0978 (19)* | 0.6 |
F25 | 0.8441 (10) | 0.8478 (7) | 0.396 (2) | 0.0978 (19)* | 0.6 |
F26 | 0.6985 (10) | 0.8939 (7) | 0.548 (2) | 0.0978 (19)* | 0.6 |
O90 | 0.8075 (9) | 0.5064 (8) | 0.520 (3) | 0.066 (6)* | 0.5 |
C91 | 0.746 (2) | 0.4862 (10) | 0.754 (3) | 0.126 (10)* | 0.5 |
H91A | 0.7806 | 0.4587 | 0.7596 | 0.188* | 0.5 |
H91B | 0.6956 | 0.4745 | 0.7697 | 0.188* | 0.5 |
H91C | 0.7586 | 0.5100 | 0.8350 | 0.188* | 0.5 |
C90 | 0.7521 (10) | 0.5095 (4) | 0.599 (2) | 0.126 (10)* | 0.5 |
C92 | 0.6893 (17) | 0.5377 (10) | 0.534 (5) | 0.126 (10)* | 0.5 |
H92A | 0.6432 | 0.5200 | 0.5533 | 0.188* | 0.5 |
H92B | 0.6962 | 0.5421 | 0.4218 | 0.188* | 0.5 |
H92C | 0.6870 | 0.5696 | 0.5853 | 0.188* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0534 (15) | 0.0331 (13) | 0.0246 (11) | 0.000 | 0.0046 (13) | 0.000 |
C1 | 0.055 (8) | 0.054 (9) | 0.036 (6) | −0.007 (7) | 0.017 (6) | −0.010 (6) |
C2 | 0.051 (8) | 0.072 (10) | 0.039 (8) | −0.006 (7) | 0.007 (6) | −0.010 (8) |
C3 | 0.052 (7) | 0.066 (9) | 0.028 (5) | −0.003 (6) | 0.008 (6) | −0.006 (9) |
C4 | 0.053 (8) | 0.048 (8) | 0.026 (6) | −0.004 (6) | 0.001 (6) | 0.003 (6) |
C5 | 0.046 (7) | 0.047 (8) | 0.024 (6) | 0.002 (6) | 0.001 (5) | −0.003 (5) |
C6 | 0.039 (7) | 0.038 (7) | 0.020 (5) | 0.001 (5) | 0.001 (5) | 0.001 (5) |
C7 | 0.059 (9) | 0.052 (8) | 0.034 (6) | −0.009 (6) | 0.000 (6) | 0.009 (6) |
C8 | 0.055 (11) | 0.032 (9) | 0.044 (10) | 0.000 | −0.011 (12) | 0.000 |
C12 | 0.036 (7) | 0.082 (11) | 0.033 (6) | −0.013 (7) | 0.004 (6) | 0.004 (7) |
C13 | 0.040 (7) | 0.083 (8) | 0.046 (8) | −0.017 (8) | 0.006 (6) | −0.010 (7) |
C14 | 0.035 (7) | 0.091 (9) | 0.056 (9) | −0.004 (8) | 0.008 (7) | 0.004 (8) |
C15 | 0.029 (7) | 0.080 (11) | 0.053 (8) | −0.002 (7) | −0.001 (6) | 0.011 (8) |
C16 | 0.033 (6) | 0.050 (8) | 0.036 (6) | −0.007 (6) | 0.002 (5) | −0.003 (6) |
C17 | 0.046 (7) | 0.042 (8) | 0.027 (5) | −0.006 (6) | 0.004 (5) | −0.008 (5) |
C18 | 0.039 (7) | 0.046 (8) | 0.039 (7) | 0.005 (6) | 0.004 (6) | 0.002 (5) |
C19 | 0.042 (10) | 0.035 (9) | 0.060 (11) | 0.000 | −0.003 (12) | 0.000 |
C20 | 0.045 (10) | 0.057 (12) | 0.059 (12) | 0.000 | 0.012 (13) | 0.000 |
C21 | 0.053 (9) | 0.054 (9) | 0.066 (11) | 0.008 (7) | 0.005 (8) | 0.003 (8) |
C22 | 0.065 (10) | 0.044 (8) | 0.105 (16) | 0.012 (7) | 0.011 (10) | 0.002 (9) |
N1 | 0.057 (7) | 0.039 (6) | 0.022 (5) | −0.002 (5) | 0.002 (5) | −0.004 (4) |
N2 | 0.051 (8) | 0.035 (7) | 0.020 (6) | 0.000 | −0.005 (8) | 0.000 |
N4 | 0.049 (8) | 0.047 (8) | 0.027 (7) | 0.000 | −0.010 (8) | 0.000 |
N5 | 0.047 (6) | 0.038 (6) | 0.030 (5) | −0.007 (5) | 0.007 (5) | 0.001 (4) |
N6 | 0.061 (11) | 0.032 (9) | 0.116 (15) | 0.000 | 0.007 (14) | 0.000 |
C109 | 0.075 (13) | 0.029 (9) | 0.042 (9) | 0.000 | −0.003 (13) | 0.000 |
C110 | 0.069 (15) | 0.046 (12) | 0.060 (14) | 0.004 (10) | −0.017 (13) | −0.012 (12) |
C111 | 0.086 (18) | 0.046 (12) | 0.052 (16) | −0.001 (11) | 0.002 (14) | −0.005 (14) |
N13 | 0.132 (18) | 0.034 (10) | 0.075 (12) | 0.000 | −0.027 (16) | 0.000 |
C209 | 0.075 (13) | 0.029 (9) | 0.042 (9) | 0.000 | −0.003 (13) | 0.000 |
C210 | 0.069 (15) | 0.046 (12) | 0.060 (14) | 0.004 (10) | −0.017 (13) | −0.012 (12) |
C211 | 0.086 (18) | 0.046 (12) | 0.052 (16) | −0.001 (11) | 0.002 (14) | −0.005 (14) |
N23 | 0.132 (18) | 0.034 (10) | 0.075 (12) | 0.000 | −0.027 (16) | 0.000 |
Mn1—N1 | 2.210 (10) | C21—C22 | 1.37 (2) |
Mn1—N2 | 2.180 (13) | C21—H21 | 0.9500 |
Mn1—N4 | 2.187 (14) | C22—N6 | 1.351 (18) |
Mn1—N5 | 2.247 (11) | C22—H22 | 0.9500 |
Mn1—N1i | 2.210 (10) | N2—C6i | 1.353 (13) |
Mn1—N5i | 2.247 (11) | N4—C17i | 1.361 (15) |
C1—N1 | 1.358 (16) | N6—C22i | 1.351 (18) |
C1—C2 | 1.384 (18) | C109—C110 | 1.41 (3) |
C1—H1 | 0.9500 | C109—C110i | 1.41 (3) |
C2—C3 | 1.379 (19) | C110—C111 | 1.35 (4) |
C2—H2 | 0.9500 | C110—H110 | 0.9500 |
C3—C4 | 1.372 (18) | C111—N13 | 1.27 (3) |
C3—H3 | 0.9500 | C111—H111 | 0.9500 |
C4—C5 | 1.366 (16) | N13—C111i | 1.27 (4) |
C4—H4 | 0.9500 | C209—C210i | 1.40 (3) |
C5—N1 | 1.370 (16) | C209—C210 | 1.40 (3) |
C5—C6 | 1.480 (15) | C210—C211 | 1.29 (4) |
C6—N2 | 1.353 (13) | C210—H210 | 0.9500 |
C6—C7 | 1.387 (18) | C211—N23 | 1.46 (3) |
C7—C8 | 1.364 (16) | C211—H211 | 0.9500 |
C7—H7 | 0.9500 | N23—C211i | 1.46 (3) |
C8—C7i | 1.364 (16) | P1—F14 | 1.594 (7) |
C8—C109 | 1.50 (2) | P1—F16 | 1.594 (7) |
C8—C209 | 1.50 (2) | P1—F11 | 1.594 (7) |
C12—C13 | 1.38 (2) | P1—F13 | 1.594 (7) |
C12—N5 | 1.380 (16) | P1—F12 | 1.594 (7) |
C12—H12 | 0.9500 | P1—F15 | 1.594 (7) |
C13—C14 | 1.34 (2) | P2—F22 | 1.54 (2) |
C13—H13 | 0.9500 | P2—F26 | 1.557 (19) |
C14—C15 | 1.42 (2) | P2—F21 | 1.578 (19) |
C14—H14 | 0.9500 | P2—F24 | 1.62 (2) |
C15—C16 | 1.386 (18) | P2—F23 | 1.634 (19) |
C15—H15 | 0.9500 | P2—F25 | 1.644 (19) |
C16—N5 | 1.326 (16) | O90—C90 | 1.209 (4) |
C16—C17 | 1.517 (17) | C91—C90 | 1.481 (4) |
C17—C18 | 1.344 (18) | C91—H91A | 0.9800 |
C17—N4 | 1.361 (15) | C91—H91B | 0.9800 |
C18—C19 | 1.408 (16) | C91—H91C | 0.9800 |
C18—H18 | 0.9500 | C90—C92 | 1.482 (4) |
C19—C18i | 1.408 (16) | C92—H92A | 0.9800 |
C19—C20 | 1.44 (3) | C92—H92B | 0.9800 |
C20—C21i | 1.437 (17) | C92—H92C | 0.9800 |
C20—C21 | 1.437 (17) | ||
N1—Mn1—N1i | 144.8 (5) | C6i—N2—C6 | 119.3 (14) |
N1—Mn1—N2 | 72.4 (3) | C6i—N2—Mn1 | 120.4 (7) |
N1—Mn1—N4 | 107.6 (3) | C6—N2—Mn1 | 120.4 (7) |
N1—Mn1—N5 | 93.5 (4) | C17i—N4—C17 | 118.3 (15) |
N1—Mn1—N5i | 97.0 (4) | C17i—N4—Mn1 | 120.9 (7) |
N2—Mn1—N4 | 180.0 | C17—N4—Mn1 | 120.9 (7) |
N2—Mn1—N5 | 107.7 (3) | C16—N5—C12 | 118.6 (12) |
N4—Mn1—N5 | 72.3 (3) | C16—N5—Mn1 | 117.6 (8) |
N5—Mn1—N5i | 144.7 (5) | C12—N5—Mn1 | 123.4 (9) |
N2—Mn1—N1i | 72.4 (3) | C22—N6—C22i | 117.6 (17) |
N4—Mn1—N1i | 107.6 (3) | C110—C109—C110i | 116 (3) |
N2—Mn1—N5i | 107.7 (3) | C110—C109—C8 | 121.9 (14) |
N4—Mn1—N5i | 72.3 (3) | C110i—C109—C8 | 121.9 (14) |
N1i—Mn1—N5i | 93.5 (4) | C111—C110—C109 | 115 (3) |
N1—C1—C2 | 122.8 (14) | C111—C110—H110 | 122.5 |
N1—C1—H1 | 118.6 | C109—C110—H110 | 122.5 |
C2—C1—H1 | 118.6 | N13—C111—C110 | 132 (3) |
C3—C2—C1 | 117.5 (14) | N13—C111—H111 | 114.1 |
C3—C2—H2 | 121.3 | C110—C111—H111 | 114.1 |
C1—C2—H2 | 121.3 | C111—N13—C111i | 110 (3) |
C4—C3—C2 | 120.9 (14) | C210i—C209—C210 | 125 (3) |
C4—C3—H3 | 119.6 | C210i—C209—C8 | 117.3 (13) |
C2—C3—H3 | 119.6 | C210—C209—C8 | 117.3 (13) |
C5—C4—C3 | 119.2 (13) | C211—C210—C209 | 114 (3) |
C5—C4—H4 | 120.4 | C211—C210—H210 | 123.1 |
C3—C4—H4 | 120.4 | C209—C210—H210 | 123.1 |
C4—C5—N1 | 121.8 (12) | C210—C211—N23 | 131 (3) |
C4—C5—C6 | 124.3 (12) | C210—C211—H211 | 114.7 |
N1—C5—C6 | 113.9 (11) | N23—C211—H211 | 114.7 |
N2—C6—C7 | 120.3 (11) | C211i—N23—C211 | 106 (3) |
N2—C6—C5 | 114.4 (11) | F14—P1—F16 | 90.00 (6) |
C7—C6—C5 | 125.2 (10) | F14—P1—F11 | 90.00 (6) |
C8—C7—C6 | 121.3 (12) | F16—P1—F11 | 90.00 (6) |
C8—C7—H7 | 119.4 | F14—P1—F13 | 90.00 (6) |
C6—C7—H7 | 119.4 | F16—P1—F13 | 90.00 (6) |
C7i—C8—C7 | 117.5 (16) | F11—P1—F13 | 180.00 (10) |
C7i—C8—C109 | 121.2 (8) | F14—P1—F12 | 180.0 (3) |
C7—C8—C109 | 121.2 (8) | F16—P1—F12 | 90.00 (6) |
C7i—C8—C209 | 121.2 (8) | F11—P1—F12 | 90.00 (6) |
C7—C8—C209 | 121.2 (8) | F13—P1—F12 | 90.00 (6) |
C13—C12—N5 | 119.9 (14) | F14—P1—F15 | 90.00 (6) |
C13—C12—H12 | 120.1 | F16—P1—F15 | 180.0 (10) |
N5—C12—H12 | 120.1 | F11—P1—F15 | 90.00 (6) |
C14—C13—C12 | 121.8 (14) | F13—P1—F15 | 90.00 (6) |
C14—C13—H13 | 119.1 | F12—P1—F15 | 90.00 (6) |
C12—C13—H13 | 119.1 | F22—P2—F26 | 92.5 (11) |
C13—C14—C15 | 119.1 (15) | F22—P2—F21 | 105.8 (12) |
C13—C14—H14 | 120.5 | F26—P2—F21 | 91.9 (10) |
C15—C14—H14 | 120.5 | F22—P2—F24 | 168.3 (12) |
C16—C15—C14 | 116.9 (15) | F26—P2—F24 | 89.7 (11) |
C16—C15—H15 | 121.5 | F21—P2—F24 | 85.7 (10) |
C14—C15—H15 | 121.5 | F22—P2—F23 | 86.1 (11) |
N5—C16—C15 | 123.6 (12) | F26—P2—F23 | 90.6 (11) |
N5—C16—C17 | 116.1 (11) | F21—P2—F23 | 167.8 (12) |
C15—C16—C17 | 120.3 (13) | F24—P2—F23 | 82.4 (10) |
C18—C17—N4 | 122.1 (12) | F22—P2—F25 | 89.0 (11) |
C18—C17—C16 | 125.6 (12) | F26—P2—F25 | 178.5 (12) |
N4—C17—C16 | 112.2 (11) | F21—P2—F25 | 87.5 (10) |
C17—C18—C19 | 120.6 (13) | F24—P2—F25 | 88.9 (10) |
C17—C18—H18 | 119.7 | F23—P2—F25 | 89.7 (10) |
C19—C18—H18 | 119.7 | C90—C91—H91A | 109.5 |
C18i—C19—C18 | 116.3 (16) | C90—C91—H91B | 109.5 |
C18i—C19—C20 | 121.8 (8) | H91A—C91—H91B | 109.5 |
C18—C19—C20 | 121.8 (8) | C90—C91—H91C | 109.5 |
C21i—C20—C21 | 115.5 (18) | H91A—C91—H91C | 109.5 |
C21i—C20—C19 | 122.2 (9) | H91B—C91—H91C | 109.5 |
C21—C20—C19 | 122.2 (9) | O90—C90—C91 | 122 (3) |
C22—C21—C20 | 119.7 (15) | O90—C90—C92 | 118 (2) |
C22—C21—H21 | 120.1 | C91—C90—C92 | 120 (3) |
C20—C21—H21 | 120.1 | C90—C92—H92A | 109.5 |
N6—C22—C21 | 123.7 (15) | C90—C92—H92B | 109.5 |
N6—C22—H22 | 118.1 | H92A—C92—H92B | 109.5 |
C21—C22—H22 | 118.1 | C90—C92—H92C | 109.5 |
C1—N1—C5 | 117.7 (11) | H92A—C92—H92C | 109.5 |
C1—N1—Mn1 | 123.3 (9) | H92B—C92—H92C | 109.5 |
C5—N1—Mn1 | 118.9 (8) | ||
N1—C1—C2—C3 | −2 (2) | C4—C5—N1—C1 | −2 (2) |
C1—C2—C3—C4 | 1 (2) | C6—C5—N1—C1 | 178.3 (11) |
C2—C3—C4—C5 | −1 (2) | C4—C5—N1—Mn1 | 179.1 (10) |
C3—C4—C5—N1 | 1 (2) | C6—C5—N1—Mn1 | −0.5 (15) |
C3—C4—C5—C6 | −179.0 (12) | C7—C6—N2—C6i | 0.0 (8) |
C4—C5—C6—N2 | −179.5 (11) | C5—C6—N2—C6i | −179.6 (11) |
N1—C5—C6—N2 | 0.1 (15) | C7—C6—N2—Mn1 | 180.0 (8) |
C4—C5—C6—C7 | 1 (2) | C5—C6—N2—Mn1 | 0.4 (11) |
N1—C5—C6—C7 | −179.5 (12) | C18—C17—N4—C17i | 0.2 (8) |
N2—C6—C7—C8 | 0.1 (17) | C16—C17—N4—C17i | −177.4 (11) |
C5—C6—C7—C8 | 179.6 (10) | C18—C17—N4—Mn1 | −179.8 (9) |
C6—C7—C8—C7i | 0.0 (8) | C16—C17—N4—Mn1 | 2.6 (11) |
C6—C7—C8—C109 | 180.0 (8) | C15—C16—N5—C12 | −3.8 (19) |
C6—C7—C8—C209 | 180.0 (8) | C17—C16—N5—C12 | 177.4 (10) |
N5—C12—C13—C14 | 1 (2) | C15—C16—N5—Mn1 | 169.0 (10) |
C12—C13—C14—C15 | −1 (2) | C17—C16—N5—Mn1 | −9.8 (13) |
C13—C14—C15—C16 | −1 (2) | C13—C12—N5—C16 | 1.5 (17) |
C14—C15—C16—N5 | 4 (2) | C13—C12—N5—Mn1 | −170.9 (9) |
C14—C15—C16—C17 | −177.6 (12) | C21—C22—N6—C22i | 0.4 (14) |
N5—C16—C17—C18 | −172.7 (12) | C7i—C8—C109—C110 | −64.7 (18) |
C15—C16—C17—C18 | 8.5 (19) | C7—C8—C109—C110 | 115.3 (18) |
N5—C16—C17—N4 | 4.9 (14) | C7i—C8—C109—C110i | 115.3 (18) |
C15—C16—C17—N4 | −174.0 (10) | C7—C8—C109—C110i | −64.7 (18) |
N4—C17—C18—C19 | −0.5 (17) | C110i—C109—C110—C111 | 2 (2) |
C16—C17—C18—C19 | 176.9 (10) | C8—C109—C110—C111 | −178 (2) |
C17—C18—C19—C18i | 0.2 (8) | C109—C110—C111—N13 | −5 (6) |
C17—C18—C19—C20 | −179.8 (8) | C110—C111—N13—C111i | 3 (3) |
C18i—C19—C20—C21i | 40.0 (9) | C7i—C8—C209—C210i | 61.4 (18) |
C18—C19—C20—C21i | −140.0 (9) | C7—C8—C209—C210i | −118.6 (18) |
C18i—C19—C20—C21 | −140.0 (9) | C7i—C8—C209—C210 | −118.6 (18) |
C18—C19—C20—C21 | 40.0 (9) | C7—C8—C209—C210 | 61.4 (18) |
C21i—C20—C21—C22 | 0.4 (12) | C210i—C209—C210—C211 | −2 (3) |
C19—C20—C21—C22 | −179.6 (12) | C8—C209—C210—C211 | 178 (3) |
C20—C21—C22—N6 | −1 (3) | C209—C210—C211—N23 | 5 (6) |
C2—C1—N1—C5 | 3 (2) | C210—C211—N23—C211i | −3 (3) |
C2—C1—N1—Mn1 | −178.6 (10) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···F25ii | 0.95 | 2.31 | 3.23 (3) | 162 |
C15—H15···O90ii | 0.95 | 2.58 | 3.53 (3) | 177 |
C18—H18···O90iii | 0.95 | 2.57 | 3.50 (2) | 168 |
C18—H18···O90ii | 0.95 | 2.53 | 3.47 (2) | 169 |
C22—H22···F21iv | 0.95 | 2.47 | 3.42 (2) | 175 |
Symmetry codes: (ii) x−1/2, −y+3/2, −z+1; (iii) x−1/2, y+1/2, z; (iv) −x+1, −y+2, z+1/2. |
D—X···A | X···A | D—X···A |
C13—H13···Cg1vi | 2.83 | 152 |
P1A—F5A···Cg2 | 3.108 (8) | 129.0 (4) |
P2A—F12A···Cg3vii | 2.906 (9) | 131.0 (4) |
Cg···Cg | Cg···Cg | |
Cg4···Cg5 | 3.779 (3) | |
Cg5···Cg6i | 3.778 (3) |
Symmetry codes: (i) -x+1, -y+1, -z; (vi) x,1/2-y,-1/2+z; (vii) x,1/2-y,1/2+z. Cg1: centroid of {N5, C21–C25}; Cg2: centroid of {N2, C6–C10}; Cg3: centroid of {N6, C26–C30}; Cg4: centroid of {N1, C1–C5}; Cg5: centroid of {N3, C11–C15}; Cg6: centroid of {N4, C16–C20}. |
D—X···A | X···A | D—X···A |
C2—H2···Cg1v | 2.72 | 156 |
P2—F25···Cg2vi | 3.091 (18) | 153.0 (10) |
Cg···Cg | Cg···Cg | |
Cg3···Cg3vii | 3.539 (7) |
Symmetry codes: (v) x, y,z+1; (vi) -x+3/2,-y+3/2,z-1/2; (vii) -x+1,y,-z+5/2. Cg1: centroid of {N5, C12-C16}; Cg2: centroid of {N2, C6-C8, C6i, C7i}; Cg3: centroid of {N1, C1-C5}; |
Metal Center | Anion | CCDC code | Reference | Space Group |
Fe2+ | PF6- | KITFEZ | Beves, Dunphy, et al.,(2008) | I41/a |
Fe2+ | ClO4- | OFUKAC | Beves, Bray, et al., (2008) | P1 |
Fe2+ | SCN- | UGEKEX | Morsali et al. (2009) | P1 |
Fe2+ | NO3- | WOMXAX | Constable et al. (2000) | P1 |
Fe2+ | ClO4- | XIQFEJ | (a) | P21/c |
Fe2+ | [Fe(SCN)6]3- | XIQFIN | (a) | Pbcn |
Fe2+ | [Fe(SCN)6]3- | XISWUS | (a) | Pbcn |
Co2+ | NO3- | VEYGIQ | Indumathy et al. (2007) | P1 |
Co3+ | ClO4- | VEYGEM | Indumathy et al. (2007) | P1 |
Ni2+ | NO3- | OFUJUV | Beves, Bray et al. (2008) | P1 |
Cu2+ | PF6- | FIYHIF | Pitarch López et al. (2005) | P41 |
Zn2+ | NO3- | ULAFET | Ding et al. (2009) | P43 |
Zn2+ | ClO4- | BIGDEC | Mehrani et al. (2013) | C2/c |
Ru2+ | PF6- | OFUKEG | Beves, Bray, et al., (2008) | I41/a |
Ru2+ | PF6-/NO3- | OFUKIK | Beves, Bray et al. (2008) | P1 |
Ru2+ | [Fe(SCN)6]3- | OFUKOQ | Beves, Bray et al. (2008) | C2/c |
Ru2+ | PF6-/NO3- | PEHPOI | Constable et al. (2006) | P21/c |
Rh3+ | PF6- | DAHDOG | Paul et al. (2004) | P421c |
(a) Beves, Constable, Housecroft, Kepert, Neuburger et al. (2007). |
Metal 1 | Metal 2 | CCDC code | Type† | Reference |
Fe2+ | Cu2+ | GIVDEV | polymer | Beves, Constable et al. (2008) |
Fe2+ | Cu2+ | OGOTEK | 5 (linear) | Beves et al. (2009) |
Ni2+ | Co2+ | WUTTEL | polymer | Yoshida et al. (2009) |
Ni2+ | Co2+ | WUTTIP | polymer | Yoshida et al. (2009) |
Co2+ | Co2+ | WUTTOP | polymer | Yoshida et al. (2009) |
Ni2+ | Ir3+ | MITQUD | 6 (cyclic) | Liu et al. (2014) |
Ni2+ | Rh3+ | MITRAK | 6 (cyclic) | Liu et al. (2014) |
Cu2+ | Ir3+ | MITCEZ | 6 (cyclic) | Liu et al. (2014) |
Cu2+ | Rh3+ | MITCID | 6 (cyclic) | Liu et al. (2014) |
Zn2+ | Ir3+ | MITQEN | 6 (cyclic) | Liu et al. (2014) |
Zn2+ | Ir3+ | MITQIR | 6 (cyclic) | Liu et al. (2014) |
Zn2+ | Rh3+ | MITQOX | 6 (cyclic) | Liu et al. (2014) |
Ni2+ | Rh3+ | MITCOJ | 3 (linear) | Liu et al. (2014) |
Ru2+ | Ag+ | WICSIL | polymer | (b) |
"Metal 1" coordinated by Pyterpy; "Metal 2" bridging metal. † Polymer or number of metals in the oligomer and respective arrangement; (b) Beves, Constable, Housecroft, Kepert, Price et al. (2007). |
Acknowledgements
We are grateful to Fundação para a Ciência e a Tecnologia (FCT Portugal) for general financial support to CICECO (PEst-C/CTM/LA0011/2013) and the R&D project, including grant for LMOL, EXPL/QEQ-QUI/0199/2013 (FCOMP-01–0124-FEDER-041445), for postdoctoral research grant No. SFRH/BPD/63736/2009 (to JAF) and for specific funding toward the purchase of the single-crystal diffractometer.
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